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Enzymatic ring-opening polymerization (ROP) of lactides and lactone in ionic liquids and organic solvents: digging the controlling factors
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{"work":{"id":56416990,"created_at":"2021-10-07T19:03:27.354-07:00","from_world_paper_id":177413871,"updated_at":"2025-02-01T08:19:13.747-08:00","_data":{"abstract":"Certain organic solvents and ionic liquids could promote the enzymatic ring-opening polymerization of lactide.","publisher":"Royal Society of Chemistry (RSC)","ai_title_tag":"Enzymatic ROP of Lactides in Solvents","publication_name":"RSC Adv."},"document_type":"paper","pre_hit_view_count_baseline":null,"quality":"high","language":"en","title":"Enzymatic ring-opening polymerization (ROP) of lactides and lactone in ionic liquids and organic solvents: digging the controlling factors","broadcastable":false,"draft":null,"has_indexable_attachment":true,"indexable":true,"seo_quality":null}}["work"]; window.loswp.workCoauthors = [212638]; window.loswp.locale = "en"; window.loswp.countryCode = "SG"; window.loswp.cwvAbTestBucket = ""; window.loswp.designVariant = "ds_vanilla"; window.loswp.fullPageMobileSutdModalVariant = "control"; 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Zhao</a></div><div class="ds-work-card--detail"><p class="ds-work-card--detail ds2-5-body-sm">RSC Adv.</p><div class="ds-work-card--work-metadata"><div class="ds-work-card--work-metadata__stat"><span class="material-symbols-outlined" style="font-size: 20px" translate="no">visibility</span><p class="ds2-5-body-sm" id="work-metadata-view-count">…</p></div><div class="ds-work-card--work-metadata__stat"><span class="material-symbols-outlined" style="font-size: 20px" translate="no">description</span><p class="ds2-5-body-sm">10 pages</p></div><div class="ds-work-card--work-metadata__stat"><span class="material-symbols-outlined" style="font-size: 20px" translate="no">link</span><p class="ds2-5-body-sm">1 file</p></div></div><script>(async () => { const workId = 56416990; const worksViewsPath = "/v0/works/views?subdomain_param=api&work_ids%5B%5D=56416990"; const getWorkViews = async (workId) => { const response = await fetch(worksViewsPath); if (!response.ok) { throw new Error('Failed to load 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Polymerization of the four-membered-butyrolactone yielded poly(3hydroxybutyrate) in up to 89% yield with a degree of polymerization of 3-12. Polymerization of the four-membered-propiolactone, the five-membered γ-butyrolactone, and the seven-membered-caprolactone also yielded the corresponding polyesters in good yields with degrees of polymerization up to 25. Coordination catalysts, such as alumoxanes, fail in the homopolymerization of γ-butyrolactone; thus this lipase route is the first homopolymerization of γ-butyrolactone. To characterize the product polyesters, we used the method of MALDI-TOF mass spectroscopy to determine both the true molecular weight of the components and the mass of the repeat unit.</p><div class="ds-related-work--ctas"><button class="ds2-5-text-link ds2-5-text-link--inline js-swp-download-button" data-signup-modal="{"location":"wsj-grid-card-download-pdf-modal","work_title":"Lipase-Catalyzed Ring-Opening Polymerization of L-Lactide in Hydrated Ionic Liquids","attachmentId":119179268,"attachmentType":"pdf","work_url":"https://www.academia.edu/125069481/Lipase_Catalyzed_Ring_Opening_Polymerization_of_L_Lactide_in_Hydrated_Ionic_Liquids","alternativeTracking":true}"><span class="material-symbols-outlined" style="font-size: 18px" translate="no">download</span><span class="ds2-5-text-link__content">Download free PDF</span></button><a class="ds2-5-text-link ds2-5-text-link--inline js-wsj-grid-card-view-pdf" href="https://www.academia.edu/125069481/Lipase_Catalyzed_Ring_Opening_Polymerization_of_L_Lactide_in_Hydrated_Ionic_Liquids"><span class="ds2-5-text-link__content">View PDF</span><span class="material-symbols-outlined" style="font-size: 18px" translate="no">chevron_right</span></a></div></div><div class="ds-related-work--container js-wsj-grid-card" data-collection-position="1" data-entity-id="630125" data-sort-order="default"><a class="ds-related-work--title js-wsj-grid-card-title ds2-5-body-md ds2-5-body-link" href="https://www.academia.edu/630125/Enzymatic_synthesis_of_poly_l_lactide_and_poly_l_lactide_co_glycolide_in_an_ionic_liquid">Enzymatic synthesis of poly-l-lactide and poly-l-lactide-co-glycolide in an ionic liquid</a><div class="ds-related-work--metadata"><a class="js-wsj-grid-card-author ds2-5-body-sm ds2-5-body-link" data-author-id="117015" href="https://unam.academia.edu/PedroRoquero">Pedro Roquero</a></div><p class="ds-related-work--metadata ds2-5-body-xs">2010</p><div class="ds-related-work--ctas"><button class="ds2-5-text-link ds2-5-text-link--inline js-swp-download-button" data-signup-modal="{"location":"wsj-grid-card-download-pdf-modal","work_title":"Enzymatic synthesis of poly-l-lactide and poly-l-lactide-co-glycolide in an ionic liquid","attachmentId":3407801,"attachmentType":"pdf","work_url":"https://www.academia.edu/630125/Enzymatic_synthesis_of_poly_l_lactide_and_poly_l_lactide_co_glycolide_in_an_ionic_liquid","alternativeTracking":true}"><span class="material-symbols-outlined" style="font-size: 18px" translate="no">download</span><span class="ds2-5-text-link__content">Download free PDF</span></button><a class="ds2-5-text-link ds2-5-text-link--inline js-wsj-grid-card-view-pdf" href="https://www.academia.edu/630125/Enzymatic_synthesis_of_poly_l_lactide_and_poly_l_lactide_co_glycolide_in_an_ionic_liquid"><span class="ds2-5-text-link__content">View PDF</span><span class="material-symbols-outlined" style="font-size: 18px" translate="no">chevron_right</span></a></div></div><div class="ds-related-work--container js-wsj-grid-card" data-collection-position="2" data-entity-id="94948250" data-sort-order="default"><a class="ds-related-work--title js-wsj-grid-card-title ds2-5-body-md ds2-5-body-link" href="https://www.academia.edu/94948250/The_Effect_of_Solvent_Hydrophilicity_on_the_Enzymatic_Ring_Opening_Polymerization_of_L_Lactide_by_Candida_rugosa_Lipase">The Effect of Solvent Hydrophilicity on the Enzymatic Ring-Opening Polymerization of L-Lactide by Candida rugosa Lipase</a><div class="ds-related-work--metadata"><a class="js-wsj-grid-card-author ds2-5-body-sm ds2-5-body-link" data-author-id="12360209" href="https://independent.academia.edu/MisriGozan">Misri Gozan</a></div><p class="ds-related-work--metadata ds2-5-body-xs">Polymers</p><p class="ds-related-work--abstract ds2-5-body-sm">Contradictions have been reported on the effect of organic solvents, especially toluene, on enzymatic ring-opening polymerization (eROP) of L-lactide. Studies have shown that log P, a common measure of hydrophilicity, affects enzyme activity. This study examines the effect of solvents with various log P values on the eROP of L-lactide, performed using Candida rugosa lipase (CRL). N,N-dimethylacetamide (DMA), 1,2-dimethoxybenzene, 1,4-dimethoxybenzene, diphenyl ether, and dodecane were used as the organic solvents. The eROP in ionic liquid 1-butyl-3-methylimidazolium hexafluorophosphate ([BMIM][PF6]) was also conducted to compare its performance with the organic solvents. The results show that [BMIM][PF6]-mediated eROP gave better conversion and molecular weight than the organic solvent-mediated eROP. In this study, the effects of solvents hydrophilicity are discussed, including the possibility of hexafluorophosphate ion ([PF6]−) hydrolysis to occur.</p><div class="ds-related-work--ctas"><button class="ds2-5-text-link ds2-5-text-link--inline js-swp-download-button" data-signup-modal="{"location":"wsj-grid-card-download-pdf-modal","work_title":"The Effect of Solvent Hydrophilicity on the Enzymatic Ring-Opening Polymerization of L-Lactide by Candida rugosa Lipase","attachmentId":97266885,"attachmentType":"pdf","work_url":"https://www.academia.edu/94948250/The_Effect_of_Solvent_Hydrophilicity_on_the_Enzymatic_Ring_Opening_Polymerization_of_L_Lactide_by_Candida_rugosa_Lipase","alternativeTracking":true}"><span class="material-symbols-outlined" style="font-size: 18px" translate="no">download</span><span class="ds2-5-text-link__content">Download free PDF</span></button><a class="ds2-5-text-link ds2-5-text-link--inline js-wsj-grid-card-view-pdf" href="https://www.academia.edu/94948250/The_Effect_of_Solvent_Hydrophilicity_on_the_Enzymatic_Ring_Opening_Polymerization_of_L_Lactide_by_Candida_rugosa_Lipase"><span class="ds2-5-text-link__content">View PDF</span><span class="material-symbols-outlined" style="font-size: 18px" translate="no">chevron_right</span></a></div></div><div class="ds-related-work--container js-wsj-grid-card" data-collection-position="3" data-entity-id="98422783" data-sort-order="default"><a class="ds-related-work--title js-wsj-grid-card-title ds2-5-body-md ds2-5-body-link" href="https://www.academia.edu/98422783/Ring_opening_polymerization_of_lactones_and_lactides_An_organic_chemistry_lab_synthesis">Ring-opening polymerization of lactones and lactides: An organic chemistry lab synthesis</a><div class="ds-related-work--metadata"><a class="js-wsj-grid-card-author ds2-5-body-sm ds2-5-body-link" data-author-id="6584483" href="https://csbsju.academia.edu/ErinWissler">Erin Wissler</a></div><p class="ds-related-work--metadata ds2-5-body-xs">2014</p><p class="ds-related-work--abstract ds2-5-body-sm">This project analyzed the ring opening chemistry of D, L-lactide, γ-butyrolactone, valerolactone, dodecalactone and caprolactone. Starting with each of the above monomers, Sn(Oct)2,SnCl2, Zn(acac)2, ZnCL2, and AlCl3 were used as catalysts in the polymerization process. Initiators included benzyl alcohol, 2-phenylethanol and 1-butanol. The results of each reaction were analyzed by 1H-NMR and IR spectroscopy and dynamic light scattering (DLS). The results were collated to determine the most promising candidates for a student project in the teaching laboratory.</p><div class="ds-related-work--ctas"><button class="ds2-5-text-link ds2-5-text-link--inline js-swp-download-button" data-signup-modal="{"location":"wsj-grid-card-download-pdf-modal","work_title":"Ring-opening polymerization of lactones and lactides: An organic chemistry lab synthesis","attachmentId":99778667,"attachmentType":"pdf","work_url":"https://www.academia.edu/98422783/Ring_opening_polymerization_of_lactones_and_lactides_An_organic_chemistry_lab_synthesis","alternativeTracking":true}"><span class="material-symbols-outlined" style="font-size: 18px" translate="no">download</span><span class="ds2-5-text-link__content">Download free PDF</span></button><a class="ds2-5-text-link ds2-5-text-link--inline js-wsj-grid-card-view-pdf" href="https://www.academia.edu/98422783/Ring_opening_polymerization_of_lactones_and_lactides_An_organic_chemistry_lab_synthesis"><span class="ds2-5-text-link__content">View PDF</span><span class="material-symbols-outlined" style="font-size: 18px" translate="no">chevron_right</span></a></div></div><div class="ds-related-work--container js-wsj-grid-card" data-collection-position="4" data-entity-id="101925893" data-sort-order="default"><a class="ds-related-work--title js-wsj-grid-card-title ds2-5-body-md ds2-5-body-link" href="https://www.academia.edu/101925893/Investigation_of_the_influence_of_impurities_on_the_ring_opening_polymerisation_of_L_Lactide_from_biogenous_feedstock">Investigation of the influence of impurities on the ring-opening polymerisation of L-Lactide from biogenous feedstock</a><div class="ds-related-work--metadata"><a class="js-wsj-grid-card-author ds2-5-body-sm ds2-5-body-link" data-author-id="14014786" href="https://jku.academia.edu/ChristianPaulik">Christian Paulik</a></div><p class="ds-related-work--metadata ds2-5-body-xs">Journal of Polymer Research, 2020</p><p class="ds-related-work--abstract ds2-5-body-sm">In order to use a L-lactide monomer that is derived from fermentation processes it is necessary to understand, how the polymerisation process is influenced by impurities which derive from the production process. We have selected a group of likely contaminants and added them at various concentrations to the polymerisation of L-lactide using tin (II)-2-ethylhexanoate as catalyst and 2-methoxyethanol as initiator. The effect of impurities onto the global properties of the polymers such as glass transition temperature, melting point and molecular mass distribution were investigated and NMR and MALDI mass spectrometry were used to identify structural changes within the polymers. Thus, it could be shown that in reference experiments cyclic polymers and linear polymers with different starting groups are formed. Addition of ethanol and sodium carbonate showed the strongest influence on molecular masses as well as polymer structures, which could be elucidated by interpretation of the MALDI m...</p><div class="ds-related-work--ctas"><button class="ds2-5-text-link ds2-5-text-link--inline js-swp-download-button" data-signup-modal="{"location":"wsj-grid-card-download-pdf-modal","work_title":"Investigation of the influence of impurities on the ring-opening polymerisation of L-Lactide from biogenous feedstock","attachmentId":102330518,"attachmentType":"pdf","work_url":"https://www.academia.edu/101925893/Investigation_of_the_influence_of_impurities_on_the_ring_opening_polymerisation_of_L_Lactide_from_biogenous_feedstock","alternativeTracking":true}"><span class="material-symbols-outlined" style="font-size: 18px" translate="no">download</span><span class="ds2-5-text-link__content">Download free PDF</span></button><a class="ds2-5-text-link ds2-5-text-link--inline js-wsj-grid-card-view-pdf" href="https://www.academia.edu/101925893/Investigation_of_the_influence_of_impurities_on_the_ring_opening_polymerisation_of_L_Lactide_from_biogenous_feedstock"><span class="ds2-5-text-link__content">View PDF</span><span class="material-symbols-outlined" style="font-size: 18px" translate="no">chevron_right</span></a></div></div><div class="ds-related-work--container js-wsj-grid-card" data-collection-position="5" data-entity-id="98760870" data-sort-order="default"><a class="ds-related-work--title js-wsj-grid-card-title ds2-5-body-md ds2-5-body-link" href="https://www.academia.edu/98760870/Ring_opening_polymerization_of_lactide_kinetics_and_modeling">Ring opening polymerization of lactide: kinetics and modeling</a><div class="ds-related-work--metadata"><a class="js-wsj-grid-card-author ds2-5-body-sm ds2-5-body-link" data-author-id="252425677" href="https://independent.academia.edu/BIdage">Bhaskar Idage</a></div><p class="ds-related-work--metadata ds2-5-body-xs">Chemical Engineering Communications, 2019</p><p class="ds-related-work--abstract ds2-5-body-sm">The ring opening polymerization (ROP) kinetics of L-lactide was studied in bulk at 150, 160, and 180 C using stannous octoate [Sn(Oct) 2 ] catalyst and 1-pyrene butanol co-catalyst. The effect of different parameters namely, time and co-catalyst to catalyst ratio was studied on the properties of polylactide. The experimental results showed high conversion of L-lactide. The kinetics of L-lactide ROP follows the coordination insertion mechanism. The experimental results obtained were studied to account for the reversible activation, propagation, termination, and validated by modeling using MATLAB. The model developed successfully predicts the monomer conversion and the kinetics of L-lactide ROP.</p><div class="ds-related-work--ctas"><button class="ds2-5-text-link ds2-5-text-link--inline js-swp-download-button" data-signup-modal="{"location":"wsj-grid-card-download-pdf-modal","work_title":"Ring opening polymerization of lactide: kinetics and modeling","attachmentId":100024768,"attachmentType":"pdf","work_url":"https://www.academia.edu/98760870/Ring_opening_polymerization_of_lactide_kinetics_and_modeling","alternativeTracking":true}"><span class="material-symbols-outlined" style="font-size: 18px" translate="no">download</span><span class="ds2-5-text-link__content">Download free PDF</span></button><a class="ds2-5-text-link ds2-5-text-link--inline js-wsj-grid-card-view-pdf" href="https://www.academia.edu/98760870/Ring_opening_polymerization_of_lactide_kinetics_and_modeling"><span class="ds2-5-text-link__content">View PDF</span><span class="material-symbols-outlined" style="font-size: 18px" translate="no">chevron_right</span></a></div></div><div class="ds-related-work--container js-wsj-grid-card" data-collection-position="6" data-entity-id="83434734" data-sort-order="default"><a class="ds-related-work--title js-wsj-grid-card-title ds2-5-body-md ds2-5-body-link" href="https://www.academia.edu/83434734/Enzymatic_ring_opening_polymerization_ROP_of_polylactones_roles_of_non_aqueous_solvents">Enzymatic ring-opening polymerization (ROP) of polylactones: roles of non-aqueous solvents</a><div class="ds-related-work--metadata"><a class="js-wsj-grid-card-author ds2-5-body-sm ds2-5-body-link" data-author-id="212638" href="https://spanalumni.academia.edu/HuaZhao">Hua Zhao</a></div><p class="ds-related-work--metadata ds2-5-body-xs">Journal of Chemical Technology &amp; Biotechnology, 2017</p><p class="ds-related-work--abstract ds2-5-body-sm">Aliphatic polyesters such as polylactides (PLAs) and other polylactones are thermoplastic, renewable and biocompatible polymers with high potentials to replace petrochemical based synthetic polymers. A benign route for synthesizing these polyesters is through the enzymecatalyzed ring-opening polymerization (ROP) reaction; this type of enzymatic process is very sensitive to reaction conditions such as solvents, water content and temperature. This review systematically discusses the crucial roles of different solvents (such as solvent-free or in bulk, organic solvents, supercritical fluids, ionic liquids, and aqueous biphasic systems) on the degree of polymerization and polydispersity. In general, many studies suggest that hydrophobic organic solvents with minimum water contents lead to efficient enzymatic polymerization and subsequently high molecular weights of polyesters; the selection of solvents is also limited by the reaction temperature, e.g. the ROP of lactide is often conducted at above 100 °C, therefore, the solvent typically needs to have its boiling point above this temperature. The use of supercritical fluids could be limited by its scaling-up potential, while ionic liquids have exhibited many advantages include their low-volatility, high thermal stability, controllable enzyme-compatibility, and a wide range of choices. However, the fundamental and mechanistic understanding of the specific roles of ionic liquids in enzymatic ROP reactions is still lacking. Furthermore, the lipase specificity towards Land D-lactide is also surveyed, followed by the discussion of engineered lipases with improved enantioselectivity and thermal stability. In addition, the preparation of polyester-derived materials such as polyester-grafted cellulose by the enzymatic ROP method is briefly reviewed.</p><div class="ds-related-work--ctas"><button class="ds2-5-text-link ds2-5-text-link--inline js-swp-download-button" data-signup-modal="{"location":"wsj-grid-card-download-pdf-modal","work_title":"Enzymatic ring-opening polymerization (ROP) of polylactones: roles of non-aqueous solvents","attachmentId":88777720,"attachmentType":"pdf","work_url":"https://www.academia.edu/83434734/Enzymatic_ring_opening_polymerization_ROP_of_polylactones_roles_of_non_aqueous_solvents","alternativeTracking":true}"><span class="material-symbols-outlined" style="font-size: 18px" translate="no">download</span><span class="ds2-5-text-link__content">Download free PDF</span></button><a class="ds2-5-text-link ds2-5-text-link--inline js-wsj-grid-card-view-pdf" href="https://www.academia.edu/83434734/Enzymatic_ring_opening_polymerization_ROP_of_polylactones_roles_of_non_aqueous_solvents"><span class="ds2-5-text-link__content">View PDF</span><span class="material-symbols-outlined" style="font-size: 18px" translate="no">chevron_right</span></a></div></div><div class="ds-related-work--container js-wsj-grid-card" data-collection-position="7" data-entity-id="81150699" data-sort-order="default"><a class="ds-related-work--title js-wsj-grid-card-title ds2-5-body-md ds2-5-body-link" href="https://www.academia.edu/81150699/A_Study_of_L_Lactide_Ring_Opening_Polymerization_Kinetics">A Study of L-Lactide Ring-Opening Polymerization Kinetics</a><div class="ds-related-work--metadata"><a class="js-wsj-grid-card-author ds2-5-body-sm ds2-5-body-link" data-author-id="66606434" href="https://independent.academia.edu/GBozga">Grigore Bozga</a></div><p class="ds-related-work--metadata ds2-5-body-xs">Macromolecular Symposia, 2007</p><p class="ds-related-work--abstract ds2-5-body-sm">The paper presents an experimental study of L-lactide polymerization in molten state using as initiator the Stannous Octoate. The experiments were performed in a Haake mixer. The operating temperatures were between 170 and 1958C, the reaction time up to 60 min and monomer to initiator initial molecular ratio between 10 2 and 5 Á 10 3. The conversion was determined by using 1 H NMR and the molecular weights distributions by SEC. A preliminary mathematical modeling study was also performed, based on experimental data and a previously published reaction scheme.</p><div class="ds-related-work--ctas"><button class="ds2-5-text-link ds2-5-text-link--inline js-swp-download-button" data-signup-modal="{"location":"wsj-grid-card-download-pdf-modal","work_title":"A Study of L-Lactide Ring-Opening Polymerization Kinetics","attachmentId":87295649,"attachmentType":"pdf","work_url":"https://www.academia.edu/81150699/A_Study_of_L_Lactide_Ring_Opening_Polymerization_Kinetics","alternativeTracking":true}"><span class="material-symbols-outlined" style="font-size: 18px" translate="no">download</span><span class="ds2-5-text-link__content">Download free PDF</span></button><a class="ds2-5-text-link ds2-5-text-link--inline js-wsj-grid-card-view-pdf" href="https://www.academia.edu/81150699/A_Study_of_L_Lactide_Ring_Opening_Polymerization_Kinetics"><span class="ds2-5-text-link__content">View PDF</span><span class="material-symbols-outlined" style="font-size: 18px" translate="no">chevron_right</span></a></div></div><div class="ds-related-work--container js-wsj-grid-card" data-collection-position="8" data-entity-id="122294290" data-sort-order="default"><a class="ds-related-work--title js-wsj-grid-card-title ds2-5-body-md ds2-5-body-link" href="https://www.academia.edu/122294290/Organocatalytic_ring_opening_polymerization_of_l_lactide_in_bulk_A_long_standing_challenge">Organocatalytic ring-opening polymerization of l-lactide in bulk: A long standing challenge</a><div class="ds-related-work--metadata"><a class="js-wsj-grid-card-author ds2-5-body-sm ds2-5-body-link" data-author-id="43712403" href="https://independent.academia.edu/LeilaMezzasalma">Leila Mezzasalma</a></div><p class="ds-related-work--metadata ds2-5-body-xs">European Polymer Journal, 2017</p><p class="ds-related-work--abstract ds2-5-body-sm">Link to publication on Research at Birmingham portal General rights Unless a licence is specified above, all rights (including copyright and moral rights) in this document are retained by the authors and/or the copyright holders. The express permission of the copyright holder must be obtained for any use of this material other than for purposes permitted by law. • Users may freely distribute the URL that is used to identify this publication. • Users may download and/or print one copy of the publication from the University of Birmingham research portal for the purpose of private study or non-commercial research. • User may use extracts from the document in line with the concept of 'fair dealing' under the Copyright, Designs and Patents Act 1988 (?) • Users may not further distribute the material nor use it for the purposes of commercial gain. Where a licence is displayed above, please note the terms and conditions of the licence govern your use of this document. When citing, please reference the published version. Take down policy While the University of Birmingham exercises care and attention in making items available there are rare occasions when an item has been uploaded in error or has been deemed to be commercially or otherwise sensitive.</p><div class="ds-related-work--ctas"><button class="ds2-5-text-link ds2-5-text-link--inline js-swp-download-button" data-signup-modal="{"location":"wsj-grid-card-download-pdf-modal","work_title":"Organocatalytic ring-opening polymerization of l-lactide in bulk: A long standing challenge","attachmentId":116990076,"attachmentType":"pdf","work_url":"https://www.academia.edu/122294290/Organocatalytic_ring_opening_polymerization_of_l_lactide_in_bulk_A_long_standing_challenge","alternativeTracking":true}"><span class="material-symbols-outlined" style="font-size: 18px" translate="no">download</span><span class="ds2-5-text-link__content">Download free PDF</span></button><a class="ds2-5-text-link ds2-5-text-link--inline js-wsj-grid-card-view-pdf" href="https://www.academia.edu/122294290/Organocatalytic_ring_opening_polymerization_of_l_lactide_in_bulk_A_long_standing_challenge"><span class="ds2-5-text-link__content">View PDF</span><span class="material-symbols-outlined" style="font-size: 18px" translate="no">chevron_right</span></a></div></div><div class="ds-related-work--container js-wsj-grid-card" data-collection-position="9" data-entity-id="13934514" data-sort-order="default"><a class="ds-related-work--title js-wsj-grid-card-title ds2-5-body-md ds2-5-body-link" href="https://www.academia.edu/13934514/Kinetics_of_the_Ring_Opening_Polymerization_of_6_7_9_12_13_16_and_17_Membered_Lactones_Comparison_of_Chemical_and_Enzymatic_Polymerizations">Kinetics of the Ring-Opening Polymerization of 6-, 7-, 9-, 12-, 13-, 16-, and 17-Membered Lactones. Comparison of Chemical and Enzymatic Polymerizations</a><div class="ds-related-work--metadata"><a class="js-wsj-grid-card-author ds2-5-body-sm ds2-5-body-link" data-author-id="34610135" href="https://independent.academia.edu/AndrzejDuda">Andrzej Duda</a><span>, </span><a class="js-wsj-grid-card-author ds2-5-body-sm ds2-5-body-link" data-author-id="32996443" href="https://independent.academia.edu/StanislawPenczek">Stanislaw Penczek</a></div><p class="ds-related-work--metadata ds2-5-body-xs">Macromolecules, 2002</p><p class="ds-related-work--abstract ds2-5-body-sm">The kinetics of bulk polymerization of 6-, 7-, 9-, 12-, 13-, 16-, and 17-membered lactones initiated with a zinc 2-ethylhexanoate/butyl alcohol system at 100°C was studied and compared with that of lipase-catalyzed polymerization. Instantaneous concentrations of the lactone monomers were determined on the basis of the relative intensities of signals in the 1 H NMR spectra (500 MHz, CDCl3 as a solvent, room temperature) from the ω-methylene protons (-(CH2)x-1CH2OC(O)-) (where x ) 4, 5, 7, 10, 11, 14, and 15) in the lactone monomer and the polyester repeating units, respectively. Linearity of the semilogarithmic kinetic dependencies (ln([lactone]0/[lactone]) vs time), revealed a first order of propagation in monomer for all of the polymerizations studied. This kinetic behavior, pointing to the constant concentration of the involved active centers and thus to the practical elimination of termination side reaction, allowed the relative polymerization rates to be determined. The following order of polymerization rates has been obtained: 2500:330:21:0.9:1.0:0.9:1.0 for the 6-, 7-, 9-, 12-, 13-, 16-, and 17-membered lactones, respectively. The order of rates of the enzymatic polymerization, determined earlier in an independent paper, shows an inverted dependence on the ring size, namely 0.10:0.13:0.19:0.74:1.0 for the 7-, 12-, 13-, 16-, and 17-membered lactones, respectively. The resulting difference in the orders of lactone reactivities in chemical and enzymatic polymerizations is explained in terms of a difference in factors controlling polymerization rates in both processes. The ring strain, which decreases with increasing lactone size, is partially released in the transition state of the elementary reaction of the polyester chain growth, which eventually leads to faster propagation for more strained monomers in chemical polymerizations. In enzymatic polymerizations, the rate-determining step involves formation of the lactone-lipase complex. The latter reaction is promoted by the hydrophobicity of the lactone monomer, which is higher for the larger lactone rings.</p><div class="ds-related-work--ctas"><button class="ds2-5-text-link ds2-5-text-link--inline js-swp-download-button" data-signup-modal="{"location":"wsj-grid-card-download-pdf-modal","work_title":"Kinetics of the Ring-Opening Polymerization of 6-, 7-, 9-, 12-, 13-, 16-, and 17-Membered Lactones. 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class="ds-related-work--metadata ds2-5-body-xs">Polymers for Advanced Technologies, 2008</p><div class="ds-related-work--ctas"><button class="ds2-5-text-link ds2-5-text-link--inline js-swp-download-button" data-signup-modal="{"location":"wsj-grid-card-download-pdf-modal","work_title":"Lipase-catalyzed polymerization of L-lactide in ionic liquids","attachmentId":73786126,"attachmentType":"pdf","work_url":"https://www.academia.edu/60261824/Lipase_catalyzed_polymerization_of_L_lactide_in_ionic_liquids","alternativeTracking":true}"><span class="material-symbols-outlined" style="font-size: 18px" translate="no">download</span><span class="ds2-5-text-link__content">Download free PDF</span></button><a class="ds2-5-text-link ds2-5-text-link--inline js-related-work-grid-card-view-pdf" href="https://www.academia.edu/60261824/Lipase_catalyzed_polymerization_of_L_lactide_in_ionic_liquids"><span class="ds2-5-text-link__content">View PDF</span><span class="material-symbols-outlined" style="font-size: 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href="https://independent.academia.edu/MarcBria">Marc Bria</a></div><p class="ds-related-work--metadata ds2-5-body-xs">Journal of Polymer Science Part A: Polymer Chemistry, 2014</p><div class="ds-related-work--ctas"><button class="ds2-5-text-link ds2-5-text-link--inline js-swp-download-button" data-signup-modal="{"location":"wsj-grid-card-download-pdf-modal","work_title":"New acid/base salts as co-catalysts for the organocatalyzed ring opening polymerization of lactide","attachmentId":46821612,"attachmentType":"pdf","work_url":"https://www.academia.edu/26525495/New_acid_base_salts_as_co_catalysts_for_the_organocatalyzed_ring_opening_polymerization_of_lactide","alternativeTracking":true}"><span class="material-symbols-outlined" style="font-size: 18px" translate="no">download</span><span class="ds2-5-text-link__content">Download free PDF</span></button><a class="ds2-5-text-link ds2-5-text-link--inline js-related-work-grid-card-view-pdf" href="https://www.academia.edu/26525495/New_acid_base_salts_as_co_catalysts_for_the_organocatalyzed_ring_opening_polymerization_of_lactide"><span class="ds2-5-text-link__content">View PDF</span><span class="material-symbols-outlined" style="font-size: 18px" translate="no">chevron_right</span></a></div></div><div class="ds-related-work--container js-related-work-sidebar-card" data-collection-position="5" data-entity-id="78678248" data-sort-order="default"><a class="ds-related-work--title js-related-work-grid-card-title ds2-5-body-md ds2-5-body-link" href="https://www.academia.edu/78678248/University_of_Birmingham_Organocatalytic_ring_opening_polymerization_of_l_lactide_in_bulk">University of Birmingham Organocatalytic ring-opening polymerization of l- lactide in bulk</a><div class="ds-related-work--metadata"><a class="js-related-work-grid-card-author ds2-5-body-sm ds2-5-body-link" data-author-id="43712403" href="https://independent.academia.edu/LeilaMezzasalma">Leila Mezzasalma</a></div><p class="ds-related-work--metadata ds2-5-body-xs">2019</p><div class="ds-related-work--ctas"><button class="ds2-5-text-link ds2-5-text-link--inline js-swp-download-button" data-signup-modal="{"location":"wsj-grid-card-download-pdf-modal","work_title":"University of Birmingham Organocatalytic ring-opening polymerization of l- lactide in bulk","attachmentId":85641810,"attachmentType":"pdf","work_url":"https://www.academia.edu/78678248/University_of_Birmingham_Organocatalytic_ring_opening_polymerization_of_l_lactide_in_bulk","alternativeTracking":true}"><span class="material-symbols-outlined" style="font-size: 18px" translate="no">download</span><span class="ds2-5-text-link__content">Download free PDF</span></button><a class="ds2-5-text-link ds2-5-text-link--inline js-related-work-grid-card-view-pdf" href="https://www.academia.edu/78678248/University_of_Birmingham_Organocatalytic_ring_opening_polymerization_of_l_lactide_in_bulk"><span 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ds2-5-body-link" data-author-id="39374511" href="https://independent.academia.edu/UlricaEdlund">Ulrica Edlund</a></div><p class="ds-related-work--metadata ds2-5-body-xs">Chemical Reviews, 2004</p><div class="ds-related-work--ctas"><button class="ds2-5-text-link ds2-5-text-link--inline js-swp-download-button" data-signup-modal="{"location":"wsj-grid-card-download-pdf-modal","work_title":"Controlled Ring-Opening Polymerization of Lactide and Glycolide","attachmentId":42231412,"attachmentType":"pdf","work_url":"https://www.academia.edu/19171377/Controlled_Ring_Opening_Polymerization_of_Lactide_and_Glycolide","alternativeTracking":true}"><span class="material-symbols-outlined" style="font-size: 18px" translate="no">download</span><span class="ds2-5-text-link__content">Download free PDF</span></button><a class="ds2-5-text-link ds2-5-text-link--inline js-related-work-grid-card-view-pdf" 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Polymer Science Part A: Polymer Chemistry, 2008</p><div class="ds-related-work--ctas"><button class="ds2-5-text-link ds2-5-text-link--inline js-swp-download-button" data-signup-modal="{"location":"wsj-grid-card-download-pdf-modal","work_title":"Mechanism of propagation in the cationic polymerization of L,L ‐lactide","attachmentId":98111073,"attachmentType":"pdf","work_url":"https://www.academia.edu/96125999/Mechanism_of_propagation_in_the_cationic_polymerization_of_L_L_lactide","alternativeTracking":true}"><span class="material-symbols-outlined" style="font-size: 18px" translate="no">download</span><span class="ds2-5-text-link__content">Download free PDF</span></button><a class="ds2-5-text-link ds2-5-text-link--inline js-related-work-grid-card-view-pdf" href="https://www.academia.edu/96125999/Mechanism_of_propagation_in_the_cationic_polymerization_of_L_L_lactide"><span class="ds2-5-text-link__content">View PDF</span><span class="material-symbols-outlined" style="font-size: 18px" 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Commun., 2011</p><div class="ds-related-work--ctas"><button class="ds2-5-text-link ds2-5-text-link--inline js-swp-download-button" data-signup-modal="{"location":"wsj-grid-card-download-pdf-modal","work_title":"Catalytic insights into acid/base conjugates: highly selective bifunctional catalysts for the ring-opening polymerization of lactide","attachmentId":73215009,"attachmentType":"pdf","work_url":"https://www.academia.edu/59134868/Catalytic_insights_into_acid_base_conjugates_highly_selective_bifunctional_catalysts_for_the_ring_opening_polymerization_of_lactide","alternativeTracking":true}"><span class="material-symbols-outlined" style="font-size: 18px" translate="no">download</span><span class="ds2-5-text-link__content">Download free PDF</span></button><a class="ds2-5-text-link ds2-5-text-link--inline js-related-work-grid-card-view-pdf" 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class="ds-related-work--metadata ds2-5-body-xs">International Journal of Biological Macromolecules, 1999</p><div class="ds-related-work--ctas"><button class="ds2-5-text-link ds2-5-text-link--inline js-swp-download-button" data-signup-modal="{"location":"wsj-grid-card-download-pdf-modal","work_title":"Lipase-catalyzed ring-opening polymerization of lactones to polyesters and its mechanistic aspects","attachmentId":83185963,"attachmentType":"pdf","work_url":"https://www.academia.edu/75404196/Lipase_catalyzed_ring_opening_polymerization_of_lactones_to_polyesters_and_its_mechanistic_aspects","alternativeTracking":true}"><span class="material-symbols-outlined" style="font-size: 18px" translate="no">download</span><span class="ds2-5-text-link__content">Download free PDF</span></button><a class="ds2-5-text-link ds2-5-text-link--inline js-related-work-grid-card-view-pdf" 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ds2-5-body-link" data-author-id="58789608" href="https://independent.academia.edu/TerraMarieJouaneh">Terra Marie Jouaneh</a></div><p class="ds-related-work--metadata ds2-5-body-xs">Macromolecules</p><div class="ds-related-work--ctas"><button class="ds2-5-text-link ds2-5-text-link--inline js-swp-download-button" data-signup-modal="{"location":"wsj-grid-card-download-pdf-modal","work_title":"H-Bonding Organocatalysts for the Living, Solvent-Free Ring-Opening Polymerization of Lactones: Toward an All-Lactones, All-Conditions Approach","attachmentId":67024327,"attachmentType":"pdf","work_url":"https://www.academia.edu/48382526/H_Bonding_Organocatalysts_for_the_Living_Solvent_Free_Ring_Opening_Polymerization_of_Lactones_Toward_an_All_Lactones_All_Conditions_Approach","alternativeTracking":true}"><span class="material-symbols-outlined" style="font-size: 18px" translate="no">download</span><span class="ds2-5-text-link__content">Download free PDF</span></button><a class="ds2-5-text-link 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